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I've been in Hell long enough to know there is no such thing as redemption. There is only promises and bargains and tricks we play on ourselves to make us believe we're good people... I'm not a good person. I own that. And if I'm going down... I'm going out with a bang.


Malachai "Kai" Parker is a major recurring character and the main antagonist of the sixth season of The Vampire Diaries. He also appears as a recurring character in the eighth season of the series. Kai is the son of Joshua Parker and his unnamed wife, as well as the twin brother of Josette, and the the older brother of Olivia, Lucas, Joey, and three other unnamed and deceased Parker siblings. However, when his true nature as a Siphoner was revealed in adolescence, his family began to treat him poorly and referred to him as an "abomination," which, among other factors, led to him growing up to be a sociopath.

He was first seen trapped in a prison world with Damon Salvatore and Bonnie Bennett. Kai unwillingly formed an alliance with Damon and Bonnie in hopes that they could all escape the parallel dimension and return to the real world.

Eventually, after Bonnie sacrificed her chance to escape in order to ensure Damon could return to the living world, Kai and Bonnie were the only two left in Kai's metaphysical prison. Later on, he and Bonnie attempt to escape the prison world, but Bonnie stored her magic in a teddy bear and sent it back to the real world as well so he couldn't force her to help him escape. Though he was enraged by this act, Kai brought Bonnie to his childhood home in Portland, Oregon and cooked her a Thanksgiving meal. However, he later betrayed Bonnie, taking the knife his sister's magic was stored in and stabbing Bonnie in the stomach with it to gain her Bennett blood to use to escape.

Kai eventually freed himself from the 1994 prison world, after which he made it a point to antagonize the Mystic Falls Gang, as he sought to kill his surviving siblings and merge with Jo, regardless of the consequences. However, in Prayer For the Dying, his younger brother Luke attempted to merge with him instead. Kai ultimately overpowered Luke and absorbed all his magic (as well as his ability to produce and retain his own magic) during the merge. Soon after, Luke's essence also merged with Kai, passing down his emotional capability and capacity for empathy, which mellowed Kai out, making him less evil and even allowing him to briefly work with the Mystic Falls Gang as an ally. However, in A Bird in a Gilded Cage, Bonnie, who was still holding an understandable grudge toward him for the torture he put her through, left him behind in the 1903 prison world with the Heretics, a group of former Siphoner exiles from the Gemini Coven, who had been turned into witch-vampire hybrids by Lillian Salvatore sometime in the 19th and 20th centuries.

In the Season Six finale, I'm Thinking Of You All The While, Kai escaped the 1903 Prison World with the Heretics, cloaking their location from Lily in exchange for her blood so that he could be turned into a hybrid as well. He killed Jo and, seemingly, her twins at her wedding to Alaric Saltzman to avoid any competition for the role of leader of the Gemini Coven. Kai then wiped out the coven through his suicide, killing his father and other coven members in the process and thereby rendering the Gemini extinct. Kai woke up and transitioned into a witch-vampire hybrid, but was decapitated by Damon Salvatore soon after out of revenge for placing Elena in a mystical slumber until Bonnie dies.

In What Are You?, Kai is temporarily able to return from Hell, with the ringing of the Maxwell bell. Kai attempted to enter a bargain with Cade in order to remain in the living world and successfully did so by giving him Elena's coffin. Later on, he attempted to kill the last remaining Gemini witches, his nieces: Lizzie and Josie Saltzman. After he failed, he was permanently banished and imprisoned in the newly created 2018 Prison World by Bonnie, Lizzie and Josie.

Kai is a member of the Parker Family, and is the last leader of the Gemini Coven.

Early History

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Kai's family in the newspaper on May 10, 1994 after he massacred them

Malachai was born in Portland, Oregon in 1972 as the eldest son of Joshua Parker and twin brother of Jo. As a siphoner, he was shunned by his family, even revealing to Caroline that he wasn't allowed to touch anyone. As twins of the Gemini Coven, Kai and Jo were expected to merge. However, Joshua knew that Kai would win the merge given his powers, and knew that Kai could not lead the coven. Due to this, Joshua and his wife kept having children until another pair of twins was born: Liv and Luke.

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Kai attempting to merge with Jo.

Realizing this, on May 9, 1994, he decided to kill his siblings and merge with Jo. He stabbed Jo with a hunting knife to get her out of the way as he went after their siblings, but Jo managed to cloak the twins to protect them, promising to merge with him so long as Liv and Luke could live. However, she had relinquished her magic, and the coven harnessed the power of a solar eclipse to trap him in a purgatory dimension for his crimes, which kept him trapped in a snapshot of the day that he was imprisoned.

In the Prison World, Kai tried to kill himself several times, each unsuccessful. He realized that it was part of his punishment, a safeguard by the Gemini Coven to make sure that Kai didn't end his eternal imprisonment early. 

Throughout The Vampire Diaries Series

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Kai reveals himself in the Prison World

In Welcome to Paradise, after watching Damon Salvatore and Bonnie Bennett in the Prison World for some time, Kai made his presence known to them at Bell's Market in the otherworldly-Mystic Falls, when Damon encountered him after having a fight with Bonnie. After a few comments here and there, Damon lost his patience and attacked Kai, who managed to calm him down and trick him into drinking some bourbon laced with vervain. When Damon continued to fight back, Kai smashed the entire shelf of bourbon, splashing it on Damon, and told him that he had no idea which bottle he would drink, so he put vervain in all of them. The vervain weakened Damon to the point where he was not able to fight Kai off. Kai quickly made a stake out of broken patio furniture and stabbed Damon in the hand, with the intention to eventually kill him. 

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Kai is overwhelmed by Bonnie's magic

Bonnie finally arrived and she demanded that Kai leave Damon alone, but Kai quickly brought up her inability to perform magic and mentioned that he had been watching them both for months, including their fights and her failure to regain her powers. He then was about to stake Damon when Bonnie, desperate to save him, managed to regain her magic by lighting a nearby candle. Realizing she could practice witchcraft again, she told Damon to run and then lit all of the spilled bourbon on fire, creating two walls of flame around Kai. Kai tried to calm Bonnie down, but Damon came up behind him and knocked him out with another piece of patio furniture. They took him prisoner at Salvatore Boarding House, and began questioning him on why he tried to kill Damon. He finally revealed that he only did it to use fear to trigger Bonnie's magical abilities again, before admitting the most important detail—that Bonnie's magic was the key to their escape out of their dimension and back to the real world.

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Kai as Damon and Bonnie's prisoner

In Black Hole Sun, Kai remained Damon and Bonnie's prisoner and questioned why Damon thought that this day in the Dimension they were forced to relive over and over was Damon's own personal hell. asks Damon why he believes the Dimension is his own personal hell. Damon refused to tell him but Kai explained that Bonnie's magic was only one part of the equation for their escape and Damon's reasons for hating this day could be the other. After brought Kai the supplies he requested, Damon told them what had happened on May 10, 1994. Kai fell asleep druing the story but mocked Damon for killing a pregnant woman on that day. Damon threatened to kill Kai if he doesn't start explaining how to escape their world. Kai told him that they would need to harness the power of the recurring daily eclipse using a mystical relic called an Ascendant and that the last time anyone saw one was in the Pacific North-West Oregon. He went on to explain that it had belonged to his family and all they needed was a locator spell from Bonnie. When the locator spell initially failed, Kai pressed Bonnie to try again. When it worked, it revealed that the Ascendant was in Mystic Falls, in Kai's possession. An amused Kai pulled the device from his own pocket, showing that he had been testing Bonnie's magic, seeing if she would be ready to perform the spell needed to escape.

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Kai reminisces about his murdered siblings

Later, Kai looked for the right spot to channel the power of the eclipse and figured out out where they needed to be standing for the spell. On their way to the best location, Bonnie discovered a newspaper that reported a family was butchered and the only missing one was the oldest named "Malachai". Kai overheard Bonnie telling Damon about the article, and confessed that he was the Malachai the paper was referring to, explaining that he killed off most of his siblings in Coven, killing everyone but his sister, whom he only ripped out her spleen because he had "soft spot" for her. While reminiscing about the slaughter without any remorse and with apparent glee, he showed his sociopathic side. Bonnie and Damon deduced that he was a witch but Kai explained that he was a witch without any of his own magic, and that when the Gemini Coven found out what he'd done to his siblings, they banished him to the dimension as his prison, his own personal hell and a snapshot of the day he had been sent away, trapping him to relive it by himself. Realizing how dangerous Kai was, Bonnie refused to do the spell, not wanting to bring a killer like him back to the real world, no matter how badly she wanted to live. Kai countered that they would get to go back home to their friends and Kai could kill off the remnants of the coven that trapped him there, seeing it as a win-win. He then threatened Bonnie and Damon moved to protect her. Kai, seeing the eclipse ended for the day, gave up, wanting to try again tomorrow but Bonnie continued to refuse.

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Kai absorbs Bonnie's magic

Later, while having dinner, Kai overheard Damon suggest that they steal the Ascendant from Kai and ditch him, thinking it would be easy since Kai didn't have any powers. Kai entered the room and told them that he wasn't entirely without powers. He just didn't have any of his own. He revealed that he was Siphoner, a witch who couldn't generate his own magic but could temporarily absorb it from others and then use it as his own. He clasped Bonnie's wrist and his hand glowed red as he absorbed Bonnie's power. He unleashed the power on Damon, giving him an aneurysm, and presented an ultimatum: that they follow his instructions and give him a way out with them, or he would drain Bonnie's powers completely, leaving her dead, kill Damon, and perform the spell himself. Damon and Bonnie reluctantly accepted Kai's terms.

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Kai is killed

In The World Has Turned and Left Me Here, Kai met up with Damon and Bonnie in the woods in preparation for the ritual, and explained that the eclipse would happen directly overhead in perfect alignment with the Gemini constellation. He informed them that they needed to do the spell underground and let the light of the moon and the sun pour through a hole that Damon would dig up and that when the light came in, it would activate the power of the Ascendant and anyone touching the relic in the sun would be sent back to Earth. Bonnie asked to see the spell and Kai told her he would show her just before they did it before going to town to get some supplies. Kai returned to find Damon’s done digging and a suspicious Damon looked through Kai's backpack to find the supplies were materialistic mementos of 1994. Kai jokingly explained that he was excited for the future but 1994 had been him home for almost two decades, and he didn't want to be homesick. Bonnie demanded to see the spell before going into the cave, but Kai just stood patiently, knowing they had no leverage. Bonnie gave in but wanted Kai to just take her magic and do it himself then. She offered her magic to him but Kai seemed hesitant, despite his threat that he could just take all of her power and perform it himself. Kai, not wanting her to call his bluff, grabs her by the shoulders and starts siphoning her power, but wouldn't kill her, proving Bonnie correct. Bonnie realized that Kai didn't know the spell and telekinetically impaled him in the chest with an ax, killing him.

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Kai is enraged after failing to escape the Prison World

After Bonnie figured out that the prison world was created by a Bennett Witch and that only a Bennett could do the spell, she realized why Kai refused to kill her. She activated the first part of the Ascendant. Kai arrived before Bonnie and Damon could leave, shooting Bonnie in the abdomen with a crossbow. Kai told them that he’d tried to kill himself many times but couldn't as part of his punishment in the prison world. Damon and Kai struggled as a wounded Bonnie grabbed the Ascendant and uses it instead on Damon, using her magic to pin Kai down and bring Damon into the light of the eclipse. She threw the Ascendant into Damon's hands and he was transported out of the dimension. Kai watched in utter rage as the Ascendant fell to the ground and shattered, leaving a hopeless Kai screaming in rage, left in the chasm with a weakened and saddened Bonnie.

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Kai threatens Bonnie

In Do You Remember the First Time?, Kai took care of Bonnie's wound and tried to fix the Ascendant. Bonnie, however, reaffirmed that she wouldn't ever help him be released from his prison. Kai grabbed her hand and showed that she had no power over him since he could drain her of her magic with just a touch. Bonnie defended herself and stabbed Kai in the throat with a pen, temporarily killing him, as she grabbed all of the Ascendant's pieces and ran. She then proceeds to collect all of the Ascendant's pieces and runs away. Later on, Bonnie realized she was missing a piece of the Ascendant. Kai arrived, having followed her trail of blood and showed her that he had the last piece. Bonnie sent objects in the room onto Kai, slowing him down but when she got back to Damon's car, Kai grabbed her throat from the backseat and demanded she finish the spell and get them both home.

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Kai brings Bonnie her teddy bear

They went back down into the cave as the eclipse came. Kai gave Bonnie her teddy bear from her childhood, claiming it's a gift, and saying that he wanted to be better and rejoin his family. Bonnie brushed off his false claims of redemption and began the spell, but stopped in the middle. Bonnie told Kai that she didn't have her magic, and an angry Kai grabbed her to see if she's lying only to find out that he couldn't siphon any, and that her magic really was gone.. She revealed that she stashed it away somewhere safe. As soon as Kai realized that she had put her magic inside her teddy bear, he discovered it was too late and that the bear had already been sent back to the real world with Bonnie's magic inside. He approached Bonnie threateningly as she told him that without magic, they would be stuck there together forever.

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Kai finds the last remaining magic in the Prison World before making his escape

In Fade Into You, Kai drove a bound Bonnie to his family's home in Oregon, where he grew up. Kai made Bonnie Thanksgiving dinner and pretended to be friendly with her, even claiming that after this one last meal, they would go their separate ways, and each take a hemisphere of the prison world. As they ate, he told Bonnie all about his dark history; the murder of his siblings, his attempt to merge with his twin, and his family imprisoning him. Through his recollections Kai realized that his twin sister, Jo had placed her magic in an object much like Bonnie had. He found the magic-imbued knife she had left in a tree stump on the Parker family's property. Kai absorbed the magic that had been concealed in the weapon and then proceeded to stab Bonnie with the knife, revealing that he knew he only needed Bennett blood to complete the spell. He left a wounded Bonnie behind, taking Damon's car, and finally escaped the prison world after eighteen years of being trapped.

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Kai finds Liv

In I Alone, Kai was in the real world, and rode in the backseat of a taxi, complaining about some of the changes in modern times. When he reached his destination, he murdered the driver with a pair of headphones, and then went into the bar where his long lost little sister,Liv worked at. Kai asked Liv for a drink, and she didn't recognize him after eighteen years. He showed her his ID, and asked her to look closely. When she saw his name, she was horrified and tried to flee from him, knowing he had tried to kill her and her twin, Luke when they were children. Liv backed away but Kai grabbed her and took some of her magic. As she attempted to escape, Kai pursued her and tried to kill her but Tyler arrived and pushed him pushes him over a railing. Kai fled and later reunited with Damon and met Elena. He weakened Damon and set Elena on fire. However, Damon managed to fight back and knocked Kai into Mystic Falls. Kai teased them, saying that there was a psycho loose in Mystic Falls and no vampires could stop him, because of the anti-magic border. Kai later paid Tyler a visit, offering to save Liv's life if the two could arrange a deal.

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Kai forces Jo to regain her magic

In Christmas Through Your Eyes, Kai abducted Jo at the hospital, after stabbing an innocent woman to get to her. Later, Kai brought Jo to the cemetery and met up with his siblings with Liv and Luke, who desperately wanted to escape their fate of having to take part in the Merge. They found Jo's knife in the real world, with the magic still contained inside, and Kai wanted to return Jo's magic so he and his twin sister could complete the Merge, as originally intended, with Kai more likely to emerge as the remaining twin. He brought Luke and Liv into the crypt where he had chained Jo. A distraught Jo demanded answers and Kai told her he was trying to reunite her with her magic, stabbing her repeatedly in the shoulder with the knife, to little effect. Luke intervened but Kai shoved him against the wall and reminded him that he would have killed him when he was just a little kid and had no problem doing it now. Luke left, not wanting to see the events unfold, and Kai continued to try and give Jo her magic back. Jo revealed that it was her choice to give it up and she has to choose to take it back. Kai took some of Liv's magic and started threatening her in front of Jo, until Jo finally submitted and took back the magic from the knife. Kai mocked how predictable it was that she would only get her magic back to save their little sister.

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Kai threatened by Damon and Alaric

Kai heard noises outside of the crypt and when he went out, found Damon waiting for him. Kai used his magic to throw Damon across the anti-magic border of Mystic Falls, which started to kill him. When Damon rushed back to safety, Kai stepped over the boundary, ensuring that Damon couldn't touch him. However, Alaric ambushed him from behind with a gun at his head. Jo came out of the crypt and begged them not to kill Kai, as it wasn't fair to Luke and Liv to be forced to do the Merge. She reasoned that with her returned magic, she could win and overpower Kai in the Merge, finding a less violent solution to getting rid of him. Kai smiled at the prospect. Jo managed to convince them to spare her brother, despite Damon's annoyance, and Kai was knocked out by Alaric.

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Kai absorbs the Travelers' spell over Mystic Falls

When Kai awoke, he was chained to a tombstone within Mystic Falls' border. Damon, from across the town line, threw stones at Kai. Kai inquired how this anti-magic border worked, looking around and wondering if it was a dome or a bubble over the town, pondering how high it reached and whether a vampire would die if they were in a plane flying over the town. Damon only responded by telling Kai that once he was in Hell, he could ask a bar full of dead Travelers the specifics since they cast the spell. Kai realized how big and powerful the spell must be if it took so many Travelers to cast it and then he grew quiet, much to Damon's surprise. Kai touched his hands against the ground, closing his eyes to concentrate. He could feel magic blanketing the entire town. Kai grinned at his discovery, and began to absorb the magic. While Damon and Alaric started to argue, Kai quietly dug his hands deeper into the earth and soaked in the entire spell into his body. While he took in the Travelers' magic, the chains around his wrists melted and Kai grew immensely powerful, causing the weather to intensify and technology to malfunction. By the time Damon and Alaric realized what Kai was doing, he had completely absorbed the power, deteriorating the anti-magic border and removing it from the land. He stood, more powerful than ever before, and easily subdued Alaric. When Damon tried to kill him, Kai turned invisible and left. He resurfaced that night, taking Elena hostage under an cloaking spell so that he could capture her without Damon even realizing it, despite being right in front of him.

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Kai tests his absorbed magic on Elena

In Woke Up With a Monster, Kai brought Elena to the Mystic Grill and explained that his body was overflowing with all of the magic he absorbed from the anti-magic boundary spell that blanketed Mystic Falls. He described that it was practically oozing out of him and he needed help controlling that much power. He showed her that he was already testing his power on the grill's manager, revealing that his dead body was cloaked on the table between them, much to Elena's horror. He had tried to use a cloaking spell on the manager initially but had accidentally killed him. Eventually, with enough tries, he was successful. Kai was amused by Elena's terror and brought her to Mystic Falls High School since it was empty due to winter break; a perfect place to test his new power uninterrupted. He chained Elena up and tested spells on her. In his attempts, he unintentionally melted her daylight ring. When she broke free, Kai pursued her to the school's chemistry lab. She put her hand in the sun to set it on fire and then used the lab's gas nozzle to hit Kai with a blast of flames. However, he recovered and after a few failed attempts, managed to incapacitate her with a spell that broke her neck.

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Kai's rampage is halted

Kai continued using Elena to test his powers and didn't notice that Damon and Jo had come to the school, with Jo cloaking them both with a spell. However, Jo was unable to keep up the spell after they rescued Elena, still not adjusted to having magic again. Kai saw them trying to flee and confronted them. Damon tried to face him and threw a piece of wood at him, seemingly impaling him. However, Kai appeared a few feet away, unscathed, and showed that Damon had really hit Elena, who Kai made look like himself through an illusion. While Damon rushed to Elena, Kai pursued his sister and grabbed her but was shot by an arrow from behind by Jeremy Gilbert. He tried to stand but Alaric appeared and injected Kai with a sedative, knocking him out. They took him prisoner, putting Kai in an induced coma, and decided to wait for all of the magic he absorbed to seep out of him before even attempting Jo's plan of merging with Kai.

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Kai wakes up

In Prayer For the Dying, Kai remained in his induced coma and Damon was tasked with watching over him, making sure he didn't wake while the others tried to find a way to ensure Jo overpowered Kai in the Merge. Tyler attempted to take Kai and wake him up so he would try and merge with Jo, to spare Liv of having to merge. Damon stopped Tyler but realized that Kai might be able to siphon the magic out of Elizabeth Forbes, who was rapidly dying from vampire blood accelerating her cancer. Damon decided to wake Kai himself to save the sheriff. Kai woke, with all of the magic he had absorbed having drained from him when he was sleeping. Damon directed him to the hospital to siphon the magic from Liz Forbes, hoping it would save her life. Kai, however, told Damon that there would be a fee for his services.

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Kai siphons the magic from Liz

Later, Kai went to the hospital and started siphoning the magic in Liz from her body. While he was absorbing the magic, Jo entered the room, shocked to see Kai and demanding to know why he was there. Kai greeted her happily, telling her he'd be right with her. Kai continued to siphon Liz's magic while Damon tried to explain his decision to Jo. Damon revealed Kai's price for helping Liz was that he wanted to merge with Jo that night, knowing he would overpower her and win the merge. Kai completed draining the magic from Liz but the sheriff started having a heart attack. Kai coldly acknowledged that her body couldn't take the siphoning and then disappeared when Elena demanded he fix it. Kai then broke Damon's neck in front of Jo, taking her to enact the Merge.

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Luke convinces Kai to merge with him

Kai took Jo to an empty park to perform the Merge. He threatened that if this was some kind of set up, he would do more damage to her cutting out her spleen this time. Jo called him a parasite and reminded him that he had destroyed her life, claiming that she was now going to destroy his. Kai wasn't bothered by her claim, confident that he would overpower her in the Merge. They began the ritual together until suddenly they were interrupted by Luke, who knocked Jo out. Luke then demanded that Kai merge with him instead of their sister. Kai broke into a fit of laughter, not believing it would work if they weren't twins but Luke theorized that because they shared the same parents and were technically the same age after Kai had never aged in the Prison World, that it could work. Kai refused but Luke pulled Kai toward him with magic, and convinced Kai to go through with it. They enacted the Merge, and both fell to the ground unconscious. Kai awakened alive, winning the Merge, much to Jo and Damon's horror. As a result, he could produce his own magic and became the new leader of the Gemini Coven. Kai vanished, proclaiming that he always won.

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Kai asks Damon and Elena for help

In The Day I Tried To Live, Kai arrived at the Salvatore Boarding House, interrupting Elena and Damon and them to deliver a message to Jo. When they questioned his intentions, he explained that after the Merge, once he had killed Luke and gained his powers, he also gained some of Luke's qualities, like his empathy. Kai told them that he just wanted to apologize to Jo for destroying their family and told them that he had even started crying when he was writing a letter to her, having trouble comprehending the concept of crying. Damon and Elena told him that they might deliver his message to Jo if he helped them contact Bonnie. Kai examined the broken Ascendant, hoping he could fix it but Kai revealed it was broken beyond repair, as he had intended so it could never be used against him again. Damon played to Kai's newfound empathy, and asked if they could at least send a message to Bonnie since it was her birthday. Kai seemed genuinely touched by that, and said he would try, given how he was now stronger than ever with the power of the Luke and the Gemini Coven at his disposal.

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Kai tries to fix the Ascendant

As they worked to fix the Ascendant, Kai was relieved that he still felt revolted by Damon and Elena's relationship, happy that Luke's personality being integrated into his own hadn't changed him completely. Jeremy entered the room and was unconvinced by Kai's sudden change of heart. Kai cheekily compared his personality change to Elena in reverse; since he had gained humanity while Elena had slowly lost hers. Kai told them that he wouldn't be able to send them back to the Prison World physically but could send them there in astral forms similar to ghosts, and wasn't sure if Bonnie would even be able to see them. Kai performed the spell and sent them to the Prison World. They were transported there but weren't able to be seen or touched by Bonnie. They discovered that Bonnie was going to kill herself but Kai lost his connection due to it requiring too much magic. Kai realized he could only send one of them back if they wanted to physically interact with the Prison World. They decided to send Jeremy back but Kai warned that if he wasn't able to pull Jeremy out, he'd be stuck there.

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Kai can't bring himself to kill Liv

Kai brought Jeremy back to the Prison World, focusing all his magic on one person to lessen the toll it took on his magic. However, Kai was ripped back into the real world by a fire poker being pushed through him by Liv, who wanted revenge for him killing Luke in the Merge. Liv tried to immobilize him but Kai threw a fork into her neck. He dowsed her in alcohol, taking great pleasure in the pain being inflicted, and threatened to drop a lit candle on her. However, he couldn't bring himself to do it, and couldn't understand why. He realized that it was the piece of Luke that resided in Kai now that was holding him back. He furiously smacked himself in the head trying to push himself to do it. Liv took advantage of it and stabbed Kai with a fork. Jeremy woke up and incapacitated Liv, dragging Kai into the kitchen and begging him to send him back to Bonnie. Once Jeremy had saved Bonnie, Damon fed Kai some of his blood to heal the injuries Liv had inflicted on him.

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Kai seeks help from Jo

In Let Her Go, Kai turned up at Jo's door claiming that he wasn't feeling good and coughing up blood, realizing that merging with Luke might not have been as successful as they hoped. Since he was supposed to merge with Jo, who had also been feeling ill, but hadn't, something had gone wrong. He revealed that as the new leader of the coven because of the Merge, if he died, then the whole coven would die as was always the tradition. Kai desperately pleaded for Jo to help fix him and she examined him with Alaric close by, who refused to leave Jo alone with Kai. She told Kai there was nothing wrong with him medically, and he balked at her, already realizing it was magic-related.

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Kai tells Jo that she's pregnant

Kai began to cough up more blood and grabbed Jo's wrist, accidentally absorbing some of her magic. Alaric intervened but Kai almost immediately felt better after the siphoning. He realized that he needed her magic, since he was supposed to get it during the Merge. When Jo was resistant, he reminded her and Alaric that if he died then the whole Gemini Coven would die and the prison worlds they had created would collapse. Alaric was stunned that there was more than one prison world, much to Kai's amusement. Later, Jo decided to go through with giving Kai her magic. Kai thanked her on behalf of the coven and the collapsing prison worlds. When Alaric asked him about the other ones, Kai just joked that they were probably filled with people like him. Jo stored her magic in Kai, making him even stronger and mending his illness. Kai then whispered to his sister that she was pregnant, and told her to have a good life before leaving.

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Kai with Damon at the Salvatore tomb

In The Downward Spiral, Kai went to the Salvatore family crypt at the cemetery, where Damon was checking to see if his mother's body was in her coffin, reiterating that she died of consumption in 1858. Kai, having seen the footage that Bonnie had taken of the 1903 prison world that showed Lillian Salvatore, suggested that maybe she was a vampire and that's how she still looked exactly like Damon remembered. Damon rebuked Kai, in complete disbelief at the possibility, but when they opened the coffin, they discovered it was empty. Kai watched with amusement as everything Damon knew about his mother was wrong. He then went to the Salvatore Boarding House and Damon asked if Kai could send him to the 1903 prison world. Kai said that he could, but he would need the corresponding Ascendant for that world. He knew where to find it, though, as he was the newly appointed leader of the Gemini Coven. He only asked that he be allowed to see Bonnie, so he could apologize for everything he'd done to her.

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Kai sees Bonnie again

Later, after Damon failed to get Bonnie to speak with Kai, Kai was disappointed by her decision Kai told him that he had a lead on the Ascendant, and had learned information from the Gemini arches about Damon's mother. He explained that Lily Salvatore was ambushed on a dock in New York City in 1903 by the Gemini Coven and they sent her to the prison world. He implied that she might have been on her way to see Damon, but refused to say anymore until he could speak with Bonnie. Damon and Kai turned up at a rave Bonnie was attending, looking for her, despite that she never wanted to see Kai again. They found Bonnie and Kai attempted to speak to her, wanting to apologize, but she remembered all of the pain he'd caused her and stormed out. Kai and Damon went back to the boarding house. Damon forced Kai to tell him everything he knew about his mother and why she had been imprisoned. Kai revealed that Lily was put in a prison world because she had killed over three thousand people and, like Stefan, Lillian Salvatore was a ripper. He elaborated that the Gemini Coven had intercepted her in New York Harbor so that she didn't tear through Manhattan. When Damon screamed that he'd heard enough, Kai left.

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Kai speaks with Bonnie

In A Bird in a Gilded Cage, Kai finally met with Bonnie after she was convinced by Damon. He explained how difficult it would be to find the 1903 prison world Ascendant. Since the knowledge of that dimension had been kept secret for generations, he would need to navigate old texts. Just when he made it sound impossible, he showed that he actually already had the Ascendant, laughing that it was in his pocket. He explained that he'd started looking for it the moment he heard about Lily. He said he could get her out, and now that he was the all-powerful leader of the Gemini Coven, he didn't even need to harness a celestial event for the power to get there. He admitted that he would only help if Bonnie went with them to the prison world. Bonnie refused but Kai told her she'd be safer in the prison world with him than with Caroline, who had turned off her humanity.

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Kai discovers Lily's Heretics

Kai sent himself, Bonnie, Elena, and Damon to the 1903 prison world. Bonnie and Kai stayed behind to perform a locator spell and Bonnie made it clear that she didn't believe he had changed. While Bonnie performed a locator spell, Kai continued his apology but ended up angrily grabbing Bonnie by the wrists because she wasn't listening to him. She told him that his old self was still in there, even if he had changed. They both headed toward the located Ascendant, but Bonnie wanted to get her revenge on him for hurting her and abandoning her alone in the 1994 prison world. She revealed that she wasn't leading him to the Ascendant at all, just earning his trust. She then stabbed him in the back, despite his pleas and claims that he had changed, and then left him in the prison world where he would be alone, just like he had left her. Later, Kai stumbled upon a dark cave and found it was inhabited by six desiccated vampires from Lily's den. Kai got too close to one of the vampires and one of them grabbed Kai, intending to use him as a blood bag and rejuvenate themselves.

In I Could Never Love Like That, Kai was only mentioned by Elena, when it was revealed that the vampires in the 1903 prison world were not ordinary vampires. They, like Kai, could siphon magic. Even though they had been turned into vampires they retained their ability, becoming Heretics: vampire-witch hybrids.

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Kai summons the Heretics for dinner

In I'd Leave My Happy Home For You, in the 1903 prison world, Kai made dinner for the Heretics. He had bite marks on him, showing that he had been supplying them with flesh blood to bring them back to full strength. He rang a bell to summon the vampire-witch hybrids for dinner, and smiled as they all approached. When the Heretics filed inside, he gleefully told them that it was going to be a big day, as it was time to finally escape from the prison world that they had been trapped in for over a century.

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Kai crashes Jo and Alaric's wedding

In I'll Wed You in the Golden Summertime, Kai appeared to Bonnie in her dreams. While she was running away from Lily, Bonnie crashed into Kai. She tried to cast a spell on him but realized she no longer had her magic. Kai said that it might be his fault since he was spooning her earlier and might have sleep siphoned her. He then indirectly told her that she can't keep screwing people over or else there would be consequences. During Jo and Alaric's wedding ceremony, Jo was stabbed multiple times in the lower back. As she collapsed into Alaric's arms, Kai turned off his invisibility spell and appeared behind his wound sister, bloody knife in hand. He then inflicted a massive aneurysm to all the attendants of the wedding and destroyed most of the church's windows and fixtures by producing high-frequency sound waves, turning the ceremony into complete and utter anarchy.

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Kai transitions into a Heretic

In I'm Thinking Of You All The While, with the wedding in ruins, Kai snapped both Stefan and Caroline's necks, claiming that the celebration had become family matter now. He gave Alaric his meaningless apologies for killing his bride and the twins, claiming that he didn't want competition for the leadership, and the twins were a threat to his reign. The Gemini Coven, including his father, tried to send him back to a Prison World. Before they had a chance to finish the spell, Kai stabbed himself in the neck with a piece of glass. He died, and as the leader of the Geminis, killed all of the members of the coven along with him. Shortly afterward, he woke up in transition, having drank Lily's vampire blood beforehand. He magically pulled his father over to him, licking his blood, and completing his transition into a vampire-witch hybrid, one of the Heretics.

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Kai pursues Alaric

He followed Alaric to his car, where Alaric shot Kai repeatedly, but it was useless now that he was a heretic. He explained that he could now siphon magic from his own vampirism, and convert into more magic for him to use. Before Kai could cause Alaric anymore harm, Alaric tried to kill himself, much to Kai's amusement. Tyler, a newly turned werewolf again, pounced on Kai and bit his neck, infecting him with werewolf venom. Kai managed to throw Tyler off of him and Tyler fled, leaving Kai to deal with the repercussions of the werewolf bite.

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Kai reveals his plans for Elena

At the Salvatore Boarding House, Bonnie and Matt watched a recorded message from Kai. In the recording, he happily explained that he put a sleeping spell on Elena so that she was linked to Bonnie, making it so she would only awaken if Bonnie was dead. He ended the message for Bonnie by telling her that it was all payback for what she did, leaving him behind in the prison world to rot. At the same time, Kai arrived at the hospital where Elena was unable to wake asked Damon for help with his werewolf bite. Damon refused to help him and demanded that he explained what he did to his girlfriend. After Kai explained his plan, and what his sleeping spell meant for Elena, he left.

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Kai clashes with Bonnie

Kai returned to the church, looking for blood to try and help deal with his werewolf bite. Bonnie arrived, demanding that Kai undo the spell he cast on Elena and her. When Kai refused, she broke some of his bones. Despite Bonnie's onslaught of inflicting pain on him, Kai continued to refuse to give in and realized he could heal his werewolf bite by siphoning the magic out of it. Kai did so with ease. Completely recovered, he used magic to throw Bonnie against a wall, nearly killing her.

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Kai is beheaded by Damon

As Damon arrived at the scene, Kai gave him the option of saving Bonnie's life or waking Elena up by letting Bonnie die. Damon decided to leave, leaving Kai both amused and completely perplexed that Damon could just abandon Bonnie so easily. He told Bonnie that he wanted to see Damon suffer, choosing between his girlfriend or one of his best friends. But while he was distracted trying to figure it out, Damon returned behind him and decapitated Kai, putting an end to his life.


In Best Served Cold, Kai appeared in Alaric and Jo's wedding tape.

In What Are You?, Kai surprised Damon and Alaric by showing up while they were trying to think of a way to kill Cade, and told them that he had a better idea than the one they had thought of.

In The Lies Will Catch Up To You,

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"I would write... Dear Diary"

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In It's Been a Hell of a Ride, Kai attempted to enter a bargain with Cade in order to remain in the living world and successfully did so by giving him Elena's coffin. Later on, he attempted to kill the last remaining Gemini witches, his nieces: Lizzie and Josie Saltzman. After he failed, he was permanently banished and imprisoned in the newly created 2018 Prison World by Bonnie, Lizzie and Josie.

Personality

Kai was a charmingly unstable newcomer with the unsettling ability to seem normal as the situation demands. He can be both playful and obsessive with a mix of adolescent angst, likely stemming from the fact that he was referred to as an "abomination" due to his unique magical ability. He was shown to be a psychopath originally, after merging with Luke and gaining emotions, something he himself later confessed to. This was demonstrated when he killed four of his siblings with no remorse, for no apparent reason. He also called his brother ungrateful for fighting back during his murder. Furthermore, while killing his little sister with her own magic, he commented that the irony is funny, or sad, and that he gets those emotions confused, further demonstrating his lack of ability to feel remorse. He had also stated to be perfectly happy with who he was, even finding the idea of someone changing him funny.

He appears to enjoy killing people, as he has done so when other methods could easily have been used to escape the situation. He had also used the threat of murder to manipulate people into doing what he wants.

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Kai helps to bring Bonnie back

After the merge with Luke, Kai had absorbed some of his personality and had changed. He was far less evil then he as before and even shows signs of genuine emotion, such as feeling bad/guilty for killing Luke and his other siblings. He also showed selflessness, which could be clearly seen in The Day I Tried To Live, when he was "half-dead" and yet agreed to help Jeremy to go back in the Prison World after being heavily injured from their encounter with Liv, knowing that his magic could overwhelm him and kill him in the process.

In A Bird in a Gilded Cage, when Bonnie Bennett tried to kill him, despite the fact he changed and gained some empathy towards others, he didn't try to defend himself; he simply teleported away.

Despite the fact that he was no longer the evil psychopath he once was, Bonnie, nor his coven forgave him for his actions as they believed magic couldn't completely alter another's personality. Knowing this and feeling rejected, as well as finding out that the Ascendant was destroyed (to try and prevent him from escaping) and that Jo's children (twins) could take away his leadership of the coven, he became enraged and his old personality quickly resurfaced; as in his own words, he believed that if everyone thought he was incapable of redemption, he may as well prove them right. Kai, who was already unstable to begin with, became emotionally unbalanced, cruel, sadistic, ruthless and vengeful In I'll Wed You in the Golden Summertime, he stabbed his twin sister, Josette at her wedding multiple times in the lower back, killing his sister and (apparently) the twins, because he did not want any competition in the future. In I'm Thinking Of You All The While, after he was given Lily's blood (off-screen) he killed himself to wipe out his entire coven, as revenge for trying to permanently trap him in Lillian Salvatore's Prison World. Also, instead of killing Bonnie when he had the chance, he linked Elena's slumber with Bonnie's life, until the day the latter dies, as he believed she 'betrayed' him for being left in the prison world and told her it was "all your fault".

After becoming a non-original witch-vampire hybrid, Kai's emotions were heightened, including his negative traits; he became more cruel, sadistic, ruthless and vengeful, he also had a sadistic sense of humor, as he found Bonnie's emotional pain very amusing.

Powers and Abilities

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As revealed in Black Hole Sun, Kai had demonstrated that he possessed the ability to absorb a witch's power and use it as his own. This can kill said witch if Kai were to drain all of the witch's power for his needs. Aside from this ability, Kai has no other magical powers of his own, and can only practice magic by stealing the magical power of others. In Christmas Through Your Eyes, Kai absorbed the power of the Traveler's anti-magic spell on Mystic Falls, showing he can absorb power from active spells as well. 

Despite having no magical power of his own, he does have the tendency to simply appear out of nowhere when he's being talked about. An example would be when Damon suggested to Bonnie to steal the Ascendant and leave without him, and Kai just appearing in the hallway. Another example would be in Do You Remember the First Time?, when Bonnie attacks him with magic, and runs out to Damon's car, only for Kai to appear in the backseat.

He also demonstrated his coven's ability to turn invisible during his confrontation with Damon and Elena but only when he absorbed another witch's power.

Despite having no magical power of his own, he appears to have paid attention during his coven's teachings, as he was quickly able to use his powers to cast spells, showing that he has the knowledge required.
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In addition to having the ability to siphon magic, Kai can sense magic in others, but this power was limited to being close enough to touch the person he intends on sensing the power on.

However, the little time he had spent practicing magic has caused him to not be able to focus his abilities very well. It took him a few tries before he could get spells to do what they were supposed to do, however, after that he is capable of easily using them.

After Kai merged with his younger brother Luke his powers grew stronger, which gave him access to Luke's magic permanently. With his new-found powers after "The Merge", he considers himself mega powerful as the new leader of the Gemini Coven. Kai's recent spell was powerful enough to transport himself, Elena, Damon, and Jeremy to the Prison World in which Bonnie Bennett was trapped inside. However, they could not interact with Bonnie physically, and could only see her. After focusing all his magic to Jeremy, he was powerful enough to give him the ability to interact physically in the Prison World, saving Bonnie's life in the process and showing her where to get enough magic to get herself out.

As of Let Her Go, Kai's twin sister, Josette, transferred all of her magic to him making him even more powerful.

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Kai casting a spell

Despite the fact that he now possessed the power of two witches, as he was only strong enough to take two people with him to the prison world and back to the real world, however, he later overcame this limit, as he had become strong enough to take all members of the Heretics (Valerie, Malcolm, Nora, Mary Louise, Beau and Oscar) back to the real world with him, (off-screen).

He had become so powerful, he was able to escape Lillian Salvatore's Prison World only with the blood of a Bennett witch without the Ascendant, combined with a the power of a recurring celestial event such as an eclipse or an Aurora Borealis, (off-screen) something that even Bonnie was unable to do, Kai was able to cloak himself and Lillian from Matt Donovan and Bonnie Bennett, despite the latter being a very powerful witch in her own right, as Bonnie was not able to sense his presence, even Damon Salvatore, a 174 year old vampire, with heightened senses was not able to sense Kai's presence, until the latter turned off his invisibility spell.

In I'll Wed You in the Golden Summertime, Kai was shown to be more powerful than all of the members of his coven, including his father, the former leader of the Gemini Coven, as he inflicts every individual attending Alaric and Jo's wedding with massive aneurysms, and he destroys most of the church's windows and fixtures by producing high-frequency sound waves, with a simple hand gesture; while he had a knife in his left hand.

He also cast a spell to link Bonnie to Elena Gilbert, causing the latter to be in a mystical slumber and stop aging as long as Bonnie is alive, Kai placed a fail-safe on this spell; if Bonnie or any witch tries to deactivate the spell, not only will Bonnie die, but Elena will die along with her, making sure there were no loopholes in this spell.

Kai possessed all the standard powers and abilities of a non-original witch-vampire hybrid.

Weaknesses

Kai had the typical weaknesses of a siphoner.

Kai had the typical weaknesses of a witch.

Kai had the typical weaknesses of a non-original witch-vampire hybrid.

Relationships

Jo Parker

Main article: Jo and Kai
Jo and Kai Christmas

Jo and Kai grew up together as witches part of the Gemini Coven. However, Kai was deemed as somewhat of an outsider due to his species-identity of being a siphoner instead of a regular witch. Their relationship is severely strained and antagonistic due to Kai wanting to be the leader of the Gemini Coven and killing most of their siblings, with the exception of their younger twin siblings (Luke and Liv). In the end, Kai killed Jo on her own wedding day and he died on the same day as well. Kai's death ended most of the Gemini Coven. Jo hated Kai for all of the atrocities he committed against her family and her, but Kai claimed to have loved Jo in his own way despite having the personality of a psychopath.

Bonnie Bennett

Main article: Bonnie and Kai
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They first met in Season Five, after Kai attempted to kill Damon in order to reawaken Bonnie's magic. After spending time with Bonnie in his Prison World (along with Damon), Kai shaped up to be one of Bonnie’s dangerous enemies. Ever since they met and interacted in the 1994 Prison World, Bonnie loathes Kai for being a murderer. After the several murders Kai committed against other innocents (including his own family), Bonnie imprisons him in another Prison World. Bonnie did this to punish Kai for all his crimes against those she cared about and for those who were innocently killed because of Kai. Before Kai's death, he escaped with the Heretics and became one of them. Kai later spelled and linked Bonnie’s life to Elena Gilbert's. As revenge against Bonnie, Elena was forced into a magical slumber until Bonnie died a natural death in order to awaken again. In Season Eight, Kai returns from hell and decided to turn Bonnie and her friends' lives upside down once again, which included him stealing Elena's coffin. After the events of the eighth season, Bonnie imprisons Kai in yet another Prison World in 2018 and Kai is forced to listen to his most hated song for all eternity while chained to a chair in a restaurant. In the end, Bonnie got her revenge against Kai and all his wrongdoings.

Other Relationships

Appearances

Season Six

Season Seven

Season Eight

Name

  • The name Malachai is of Hebrew origin. It is a variation of the name Malachi, meaning "angel, messenger of God".
  • Other spellings of the name Malachai include Malachi, Malachie, Malachy, Malaki, Malakia, Malaquias, Malechy, Maleki, Malequi, Malakai, Malak.
  • Parker is an English family name, derived from the Old French with the meaning "keeper of the park".

Trivia

  • According to Julie Plec and Caroline Dries, he could be irredeemable.
  • Since Kai was 22 years old at the time of his imprisonment in the year 1994, he would be 40 years old in current time, which is 2013 in the show's timeline. This means that Kai would be the same age or in the same age group as most of the main characters, such as Elena, Bonnie, Caroline's etc, parents.
  • Due to the nature of his prison, he is biologically 22, but chronologically 40.
  • Kai knows about vervain, however, as revealed by him in Welcome to Paradise, Kai does not have a lot of experience with vampires. In I'm Thinking Of You All The While, he reveals he did not even know werewolves existed until he was bitten by Tyler after he re-triggered his curse.
  • He can absorb power from other witches, even to the point of killing them, if he so chooses.
    • Kai is the first witch in The Vampire Diaries/The Originals franchise with this kind of ability.
  • Kai is one of only ten recurring characters that appeared in more than 10 episodes in their inaugural season. The other eight are Anna, who appeared in 11 episodes during Season One; Elijah Mikaelson, who appeared in 12 episodes during Season Two; Rebekah Mikaelson, who appeared in 17 episodes during Season Three; Atticus Shane who appeared in 11 episodes during Season Four; Nadia Petrova, Wes Maxfield and Enzo who appeared in 12 episodes each in Season Five; Jo who appeared in 17 episodes in Season Six and Rayna Cruz who appeared in 13 episodes in Season Seven.
  • He was a member of a coven, despite his lack of magical powers, until he killed the majority of his family. As punishment, the Gemini Coven trapped him in a purgatory dimension which Kai has referred to as his own personal hell. This revelation means that Damon and Bonnie are not actually in Damon's personal hell, which they originally thought upon their arrival.
  • There are similarities between Kai and Klaus' characters:
    • They are both different from the rest of their siblings, Klaus was born werewolf then turned hybrid, Kai was born as a warlock without magic but has the ability to absorb magic, and later turned into a vampire/witch hybrid who can siphon their own vampirism to maintain constant magical powers.
    • They both have hurt most of their siblings. Although in Kai's case, he killed most of them while Klaus prefers to neutralize his.
    • They are both called with abridged versions of their full names (Malachai and Niklaus) by most people.
    • They both needed blood from girls with supernatural heritage to free themselves from magical restrictions placed on them by their family
      • Klaus - Elena's doppelgänger blood to break the hybrid cure cast on him by his mother.
      • Kai - Bonnie's Bennett blood to free himself from his Prison World that his family sent him into.
    • Their fathers feel ashamed of them and abused and rejected them as a result. This causes them to be the way they are.
    • They both become the main figure in supernatural bloodlines, and their death would kill every member of those bloodlines.
  • He has voiced his disdain for his full name, stating it was like his parents expected him to be evil. Ironically, Malachai means "Messenger Of God".
  • Kai has tried to kill himself several times since being placed in his purgatory. However, as seen in The World Has Turned and Left Me Here, Kai comes back to life every time.
  • In Fade Into You, it's revealed that he can fly a plane as he flew him and Bonnie to Portland, it's unclear if he already knew how to fly or learned to during the last 18 years in the Otherworldly Time Dimension.
  • It is implied by Julie Plec and Chris Wood himself that Kai might have a crush or a thing for Bonnie.
  • In Christmas Through Your Eyes, Kai becomes supercharged with magic after absorbing the power from the spell of Traveler magic that created the anti-magic field around the Mystic Falls.
    • He also takes Elena Gilbert prisoner at the end of the episode, having knocked her out with a tire iron.
  • He shared his father's knack for cloaking spells.
  • Kai took Elena as a prisoner to practice using magic on her in Woke Up With a Monster.
  • Kai is the first one to know about Jo being pregnant as he himself told her the news.
  • Kai's powers are reminiscent of a warlock's from Charmed. Being able to absorb magical powers through killing the person possessing them.
  • In Prayer For the Dying, Kai siphons the magic of vampire blood in Liz's system to save her from dying from the effects vampire blood has on cancer.
    • This implies that he can kill vampires by absorbing the magic of vampirism which keeps them alive or undead.
    • This also makes him the only remaining thing that could kill an immortal besides Elena and Stefan's blood in conjunction with the traveler spell, and now the cures from the two Prison World, and also an Original along with the aforementioned items and the White Oak Stake along with a powerful enough witch.
  • So far he's the only character who has never had a past or present love interest.
  • Kai is a subspecies of witches called an aberrant witch that originally only had powers when siphoning magic from a source. Jo revealed that the Gemini Coven has had many of these aberrant witches in the past, and they were turned into vampires that had witch powers. Since they didn't have power before being turned, they are a loophole in nature that are vampires with the powers of witches, with their vampirism giving them an everlasting source to siphon magic from.
  • Kai is the last character to die in Season Six.
  • He is the first known witch in the series to be a vampire's blood source.
  • He returns in I'll Wed You in the Golden Summertime by stabbing his sister in the back during her wedding to Alaric.
  • Kai is the third main antagonist to have been killed in the season he debuted in.
  • Kai is the second main antagonist to have been killed permanently in a season finale. The first was Markos.
  • Kai is the fourth vampire (witch-vampire hybrid) to be bitten by Tyler.
    • Damon (Season Two), Caroline (Season Three), and Nadia (Season Five) were bitten by Tyler.
      • Unlike others, however, Kai survives by siphoning the magic out of the bite.
        • This also makes him the first vampire to be cured of a werewolf bite without needing Klaus' blood.
  • In I'm Thinking Of You All The While, Kai revealed that he used a Bennett's blood (de facto Qetsiyah's blood) to escape from the 1903 Prison World.
  • Kai is the second character to have killed a pregnant woman. The first was Damon.
    • However, both of them have failed to killed the children.
  • He and Jenna Sommers share the distinction of being the only vampires to be shown to be in transition, feed to complete their vampirism, and die all in the same episode.
  • He was a prisoner twice; once in 1994 and once in 1903 and both had been caused and/or helped by a Bennett witch.
    • Sheila Bennett gave the Gemini Coven her blood to create 1994 while Bonnie intentionally left him in 1903 as revenge for what he did to her.
  • Kai has never met Lorenzo.
  • Kai, like Stefan Salvatore, completed his transition to vampire by feeding on the blood of his dying father, Joshua Parker, like Stefan did to his father Giuseppe. Like Stefan, he is responsible for his father's death, Kai through his suicide, whereas Stefan killed his father by accident with his vampire strength causing his father to fatally stab himself.
  • Kai has Twitter account Cobrakai1972
  • Kai, along with Klaus, Katherine and Kol, are arguably the most popular villains in The Vampire Diaries. Ironically, all their names start with the letter "K". Fans have dubbed this group of villains Team K.


Quotes

Kai (to Damon): "Rough day, huh, Damon? Sorry. Manners. I'm Kai. Nice to meet you. Pork rind?"
Kai (to Damon): "Oh, you think this is annoying? Hmm. Try listening to you and Bonnie bicker every 5 minutes."
Kai (to Damon): "Of course I have. You two are the closest thing I have a to a TV. I mean, you're no "Baywatch," but...Remember "Baywatch"? Oh. Oh, man, you got to watch it. You like lifeguards, like... Hot ones?"
Kai (to Damon): "Temper's gonna get you in trouble, Damon. It's already driven Bonnie away how many times? Oh, oh, oh, wait. I know. 13."
Kai (to Damon): "Ok. Ok. Sorry. Seriously. I'm just kind of rusty on the face-to-face type human interactions."
Kai (to Damon): "Maybe you should have a drink. That usually calms you down. Then makes you angry, then sad, then calm again. It's a weird cycle, and look, if you really want to know the reason I'm following you, it's because I want to kill you. Vervain in your bourbon. Who didn't see that one coming?"
Kai (to Damon): "Who buys patio furniture from a grocery store? I mean, somebody must. Otherwise, it... it wouldn't be here. But now I'm a little unfamiliar with vampires, but from what I've gathered, a stake in the heart should do it, right?"
Kai (to Damon): "You can always fight dirty, Damon. Like that time you and Bonnie played monopoly and you stole from the bank. Not cool."
Kai (to Bonnie): "The useless one is here. Thank God. I've watched you try to do magic for months now. What are you gonna do, fail at me? It's embarrassing. I'm embarrassed for you."
Kai (to Damon): "Let me guess. I answer right, I get a pork rind. Wrong, I get a poker."
Kai (to Bonnie and Damon): "The important thing is that you have your magic back. It worked. What, you... you didn't really think I'd kill Damon, did you? Heh heh. In what universe does that make sense? Who would kill 1/3 of our population? I'm not a monster. I knew Bonnie would show up. She always comes back, all 13 times, and I knew with the right motivation she'd be able to access her magic, although I-I did get a little worried with all your bickering that Damon's life wouldn't be enough motivation, but turns out it was. I guess that's just how you two show your love."
- Welcome to Paradise

Kai (to Bonnie and Damon): "And, of course, I broke into the Oval Office and took a picture of myself at the window, looking all JFK. But then, I was, like, "Wait-- How am I going to get these photos developed?"--"
Kai (to Bonnie and Damon): "Well, I heard you tell Bonnie this place was your own personal hell. I'm kinda curious why."
Kai (to Bonnie and Damon): "If you torture me, I'll get mad, and then I won't want to help you. What kind of person needs to have that explained to them?"
Kai (to Damon): "I was listening, in my sleep."
Kai (to Bonnie): "Ignore him, Bonnie. Pretend he's a white-noise machine. That's how I used to tune out my siblings. I grew up with a ton of little sisters and brothers. You know, all of them constantly yammering. But it taught me how to focus."
Kai (to Bonnie): "Yeah, but I wanted to feel your hand on my chest."
Kai (to Bonnie and Damon): "Who names a kid Malachai? It's like they expected me to be evil."
Kai (to Bonnie and Damon): "Hello! Not everyone died. I had a soft spot for one of my sisters. 'Cause otherwise, I would've cut her lungs out, and not just her spleen. You can survive without a spleen."
Kai (to Damon): "This place isn't your hell, Damon. It's mine."
Kai (to Bonnie): "Oh, come on, Bonnie. You wanna go home to your friends, I wanna go back and give the rest of the Gemini Coven an excruciating death. Win-win."
Kai (to Bonnie and Damon): "Here's the thing: I have a killer effect on magic. I can't generate it myself. But, I can consume it from others temporarily. My family called me an abomination. That hurt my feelings."
- Black Hole Sun

Kai (to Bonnie and Damon): "I heard my name. All good I hope."
Kai (to Bonnie and Damon): "Have you never portal-jumped through an eclipse before? Okay look, the light of the eclipse will shine down and activate the Ascendant, you spout a little witchy woo and then poof! Anyone standing in the circle of light holding the Ascendant goes home."
Kai (to Bonnie and Damon): "555-Hiya-Kai, no way I'm giving those digits up."
Kai (to Bonnie and Damon): "Look. The future sounds great, all right? I'm super excited about the Internet, but 1994 has been my home for most of my life. I'd hate to get homesick. So let's get down there--"
Kai (to Bonnie and Damon): "Forgetting someone?"
Kai (to Bonnie and Damon): "Did you really think I hadn't tried to kill myself before? Because I had-- lots of times, lots of ways."
Kai (to Bonnie and Damon about the Ascendant): "Grab that, and the next arrow goes in her heart. Your choice."
- The World Has Turned and Left Me Here

Kai (to Bonnie): "Right. Anyhoo, I have no idea how you managed to shatter the ascendant into a billion pieces, but we need to put it together before the eclipse at 12:28. You want to help? I know you're a puzzle person."
Kai (to Bonnie): "What was that? Huh? What? You're gonna do the spell and finally get us home?"
Kai (to Bonnie): "Looking for this? You stole the ascendant, naughty girl. You weren't planning on using and leaving me behind, were you? You left a trail of blood in the driveway. Figured where else would you stop and play nurse?"
Kai (to Bonnie): "I thought about taking the keys, but that'd be like taking the cheese out of a mousetrap, right, Bonnie? Although, you know, fun fact. Mice don't actually like cheese. Isn't that great? Shh, shh, shh. Shh, shh, shh. So we have an hour until the eclipse. It's time to go home, Bonnie."
Kai (to Bonnie): "I brought you a present. Ta-da! Ms. Cuddles! Thought you might want to bring her along."
Kai (to Bonnie): "I know you think I'm a monster. I mean, I did murder or heavily maim most of my immediate family, but after a long period of self-reflection, I've come to the conclusion that I could have handled my anger better."
Kai (to Bonnie): "I didn't mean it. Honestly, I would do anything to get my family back, and the thing I'm most scared of is trying to figure out how to live in the world again. Sort of hoping you've been a positive influence on me. You're a good person, Bonnie. You're brave, loyal, patient. I want to be more like you. (Kai uses a high-pitched voice for Ms. Cuddles) What do you say? Friends?"
Kai: "So long, 1994."
- Do You Remember the First Time?

Kai (to Jo): "Josette. Where are they? Oh, Jo. Come on out, Jo. I know you can hear me. Josette? Where are they, Jo? Hey. Everything's gonna be OK, all right? Everybody's just playing a game. You guys want to play a game? You want to play hide-and-seek? Shh. OK. Come on out, Jo. You know I won't kill you."
Kai (to Bonnie): "Wakey, wakey."
Kai (to Bonnie): "Get so lucky to arrive here on a private flight piloted by yours truly? Oh, you would have been super-impressed with my flying skills, but I'd already knocked you out with painkillers."
Kai (to Bonnie): "Portland, Oregon, stomping grounds of Courtney Love, Tonya Harding, and tons of other awesome people."
Kai (to Bonnie): "I've been counting eclipses since I was imprisoned on this empty planet, and according to my running tally, I've been here for 6,771 supernaturally repeating days, so in the real world, which we'll never get back to because you sent your magic away in a Teddy bear, today's my favorite day of the year. Thanksgiving. I'm cooking you dinner."
Kai (to Bonnie): "Ah. Memories. Pitter-patter of little siblings' feet, witchy-woo, chanting in the air, mom and dad calling me an abomination."
Kai (to Bonnie): "Because I can finally show it to someone. My coven goes out of their way to make sure no one finds us, but since they're not here to be paranoid freak shows, mi casa es su casa. Come on."
Kai (to Bonnie): "That smells great. Not exactly a turkey dinner, but it's what my family had in the fridge on May 10, 1994."
Kai (to Bonnie): "Don't tough that. Because it's brand-new, looks cool, and I don't want you to bust it."
Kai (to Bonnie): "I get it. I knocked you out, kidnapped you against your will. Can't you see I'm trying to apologize?"
Kai (to Bonnie): "Fine. Can we at least have one last dinner conversation before my eternity of aloneness resumes?"
Kai (to Bonnie): "In the spirit of Thanksgiving, I'll even let you take my car."
Kai (to Jo): "Where are they? (screams) Where are they?!"
Kai (to Bonnie): "Is it a crime to want to savor our last meal together?"
Kai (to Bonnie): "My family sent me to this prison world. My father, the great coven leader... he treated me like crap for 22 years and then locked me here. It's like his... like his kids didn't even matter. Coven always came first no matter what."
Kai: "Olivia, Lucas? Olivia? Lucas? Come out, come out, wherever you are."
Kai (to Jo): "Josette, what did you do? Why can't I feel your magic? And why aren't they saying anything? They should be saying something. They should be saying something, right? We're merging. This should all be a bigger deal."
- Fade Into You

Kai (to the taxi driver): "You ever worn skinny jeans? Agh. It seems wrong. I'm all bunched up. Also, why are jeans so tight when phones are so big?"
Kai (to the taxi driver): "Oh, God. I'm that guy, right? That guy that won't shut up. Oh, I hate that guy. I just sat next to that guy on the plane. He was the worst. Hey. Speaking of planes, have you flown recently? Because what's with the whole liquid situation and the stripping before you go through security thing? It's weird."
Kai (to the taxi driver): "Ok. Well, I'm sorry, but the real terrorists are some of those people taking off their shoes. I know I'm chatty. Sorry. I've just been in prison for awhile. Not like a regular prison, you know, more like a..."
Kai (to the taxi driver): "All right. Jeans. Uh, will you take this? Hang on. Hang on. I got it. Oh. Hey. Gum. Nice."
Kai: "Heh. "Liv". Ironic."
Kai (to Liv): "You on Twitter? Ah. I just signed up. You should follow me. Cobrakai1972. Come on. Like "Karate Kid"? Did you know you can follow celebrities? Heh. They all Twitter the stupidest things. It's-it's hilarious."
Kai (to Liv): "Oh. Hang on, hang on. I'm gonna get a real drink. No bourbon. I'm secure enough in my masculinity. Vodka's boring, rum's too tropical. Ooh. Tequila. You do not want to see me on Tequila. What about gin? Is that weird?"
Kai (to Liv): "No. True story, but that's not the most interesting thing on that I.D. Here. Look again. Name, address..."
Kai (to Liv): "Last time I saw you... I was trying to kill you. Why don't we pick up where we left off?"
Kai: "Life is so much easier with magic."
Kai (to Liv): "Feels kind of like cheating. I'm sad you didn't recognize me. That means dad erased all trace of my existence-- family pictures, movies, little handprint turkey I made. What a dick."
Kai (to Liv): "You were always so bad at hide-and-seek. I mean, you were 4, but still, find a better hiding spot."
Kai (to Elena and Damon): "Wait. Are you guys talking about Bonnie Bennett? Because honestly, I didn't think she was all that great."
Kai (to Damon): "Oh, hey. Me, too. Oh, yeah. Damon, I, uh, I stole some of Liv's magic when I tried to kill her. Think some of it might still be in my system, so pardon me."
Kai (to Elena and Damon): "Huh. I guess this is that, uh, anti-magic border, which means now there's a psycho loose in Mystic Falls and no vampires around to stop him. Whoops."
Kai (to Tyler): "I think gin gets a bad rap."
Kai (to Tyler): "I'd rather not kill you, but I will."
Kai (to Tyler): "This is gonna sound crazy, but I want to save Liv's life. Feel like making a deal with the devil?"
- I Alone

Kai (to Jo): "I stabbed her."
Kai (to Liv and Luke): "I know I tried to kill you when you were toddlers, but I got to say, it sure is nice to be around family for the holidays."
Kai (to Liv and Luke): "Sissy's up."
Kai (to Jo): "I haven't seen you in 18 years. You can't muster a hello?"
Kai (to Luke): "I'm trying to reunite Jo with her... (He stabs her again) magic. It's not working."
Kai (to Luke): "I was wanting to kill you when your brain was the size of an acorn. You don't think I'll do it now?"
Kai (to Jo): "Oh, so dramatic. All right. Sissy... Let's try this again."
Kai (to Liv): "I'm going to find a bandage while you figure out how to put the magic in this knife into our sister. Preferably by the time I get back so I don't have to dull it by slitting your throat."
Kai (to Jo): "Isn't it gonna be funny when I kill her using her own magic? Wait. Is that funny or sad? I get my emotions mixed up. Hey. What's the one for fire again? It's "incendia," right? Phesmatos..."
Kai (to Damon): "Oh, whoops. Looks like you found the anti-magic border. Drew a line in the dirt for everyone's convenience. See? Yeah. You're welcome."
Kai (to Damon): "So this whole anti-magic thing, is it like a... Like a dome or a bubble? Like, say, you were in 747 flying over Mystic Falls, would you die? You know, that could be dangerous, like if you're headed to New York and your pilot reroutes for weather."
Kai: "That's a lot of travelers. Must be a pretty big spell. Like a really big spell. So big... it covers every inch of an entire town."
Kai (to Elena): "I may have put a cloaking spell on us. How genius is that?"
- Christmas Through Your Eyes

Kai (to Elena): "See, we never went out to dinner when I was a kid, so, I always had this fascination with chefs and fine dining. Dad actually let me cook... Taught me to measure by eye. Seasonings to taste, all that stuff, but it's different now in the restaurant world. Everything's on time. It's like, the fries go in, you push a button, it dings and you take 'em out. Literally no guess work."
Kai (to Elena): "Uh, well I spent eighteen years in abandoned restaurants and now I'm showing off the fruits of my labor."
Kai (to Elena): "Oh, you mean like, here here, in Mystic Falls. (laughs) Sorry, I'm nervous. You're like, really pretty."
Kai (to Elena): "Well I took this spell that was keeping supernaturals out of Mystic Falls and I like absorbed it. Like ate it I guess. It’s cool, huh? First, I eat magic and then eventually I lose it. But, with a huge spell like that. I mean, come on, magic’s oozing out of me. It’s all over the place. You know, I didn’t quite realize, I was so out of control until I met the manager of the grill a few hours ago and he was all like, “Yeah, you can’t come in here, we’re closed, and you have an unconscious girl over your shoulder.” And I was like, “Don’t judge me.” So, then I gave him a heart attack. Tried to. But all I did was make him vomit uncontrollably, which was like, uh, all right, let’s stop that. So, I tried again, and I think I broke his spine. I’m not- I’m not really sure, because the third time I tried the spell, he kind of exploded in blood. Whoops."
Kai (to Elena): "I just told you, I have too much magic. You know, it wasn't until after my test run with the manager that I realized, if I start to merge with Jo and my gushing fountains of magic turn her into that guy, then I'm not gonna have a twin for the merge. So, Elena, that is why you are here. Because I need to get my magic under control. By practicing with you. Or rather, by practicing on you. Oh, PS: Silver lining, after the manager finally stopped thrashing around, I finally managed a cloaking spell. Thank you. It's easy to do and...undo. Phasmatos oculix. (Dead manager appears on table in front of Elena) Table for three. You had no idea."
Kai (to Elena): "They have plenty of restrooms, no flammable surfaces, and everyone's on winter break...Still. You know, it's no wonder America got dumb while I was locked up; they're never in school. (Looking at pictures in the trophy case of the cheerleading squad; grinning) Is that you? Oh, and there's Bonnie. You guys look so innocent. Smiling, like nothing bad could ever happen to you. Anyway, do you mind if I try to turn your blood into acid again?"
Kai (to Elena): "Take it that ring meant something to you? I never understood sentimental attachments to things, because then it's so upsetting when you lose them."
Kai: "Really? Dammit. Bingo."
Kai (to Elena): "Well, thanks. Yeah, somebody burned my other one. Which was awesome, by the way."
Kai (to Elena): "I am starting to see why Damon digs you. You are crazy-pants. Oh, it sucks about that shirt, though."
Kai (to Elena): "Oh. Is this going to be like an episode of "Ricki Lake" where I come face-to-face with my demons and change for the better?"
Kai (to Elena): "I guess I liked my brother, Joey. We played Dr. Mario together and he'd always win. Actually, one of my favorite memories is when I finally beat him. Of course, my favorite memory is when I finally beat him to death. You don't have to waste your energy trying to change me. If Ricki taught me anything, it's that liking yourself is the most important thing. And I like me."
- Woke Up With a Monster

Kai (to Damon): "You really think I'm gonna trust you?"
Kai (to first Tyler then Damon): "Hi. Let's discuss my fee."
Kai (to Elena and Damon): "I get what you two see in each other. It's very dys-fun-ctional. Ha! You see what I did, stressing the "fun" in dysfunctional."
Kai (to Jo): "Hey sis, little busy. Be with you in a jiffy."
Kai (to Elena): "Oh, that is so tragic. You know, 'cause you guys jumped through hoops to get the magic out of her system, but then her ticker's just not strong enough to take a little siphoning."
Kai (to Jo): "Magical neck snap. Never gets old. Isn't this the part where you start running?"
Kai (to Jo): "Look at those pretty planets, all twinkly and bright. Oh, Josette, you would not believe how sick I am of eclipses."
Kai (to Luke): "Fine. It’s your funeral."
Kai (to Jo): "You know, if you think I didn't spend the last 18 years in solitary thinking about you screwed me over last time, you're wrong. So if this is just another setup, I'll rip something out more important than a spleen. Like a tongue or a heart. So, any closing remarks?"
Kai: "You win some, you lose some. Except for me. I always win."
- Prayer For the Dying

Kai: "Oh! Forgot how massive this house was. Yum! Cupcakes!"
Kai (to Elena and Damon): "Funniest thing. I need your help."
Kai (to Elena and Damon): "I haven't been able to find her using the locator spell, and, you know, good on her because under normal circumstances, I’d be superjazzed to gouge out her belly button."
Kai (to Elena and Damon): "Well, in case you haven’t figured it out by now, I’m a sociopath. I know. Shocker. I like being a sociopath. You know, I’m not burdened by things like guilt or love. So then this merge happen with my brother Luke. And I won, which is just great because I absorbed his ability to do magic. But now, I can't stop thinking about how Luke died. How Liv's life is ruined. For some horrible reasons, I can't shake. I feel bad. So when I absorbed Luke's magic, I must have gotten some of his qualities or something. Like empathy. So, I googled how to process emotional pain. And they said if you write everything down in a letter and burn it, you'll heal. So I started writing, and this water literally started pooling in my eyes. As that ever happened to you? Like- like water just- just oozing out of my eyeballs like I'm some alien creature excreting fluids."
Kai (to Jeremy): "Think of it like, Elena in reverse. You know she was human, pure, dating the good Salvatore. Then she became an undead blood-vacuum, stopped caring about right and wrong, started dating the bad one... I'm sure I missed a detail or two, but I'm just paraphrasing what Damon told me in the Prison World."
Kai (to Elena and Damon): "Oh, thank God. You two together still totally revolting to me. Finally, a familiar feeling. Luke didn't take me over completely."
Kai: "You see this blood? I'm guessing that's not a good sign."
Kai: "All while sending the three of you back over there? Sure. Yeah. Hey, why don't I reanimate your dead parents for a tea party while I'm at it?"
Kai (to Liv): "Dang, sis. That was harsh."
Kai (to Liv): "It's all coming back to me, Livvie Poo. You know the charge… that race through your bones… at the prospect of watching someone burn to death? I really missed that feeling."
- The Day I Tried To Live

Kai (to Jo): "Look. There's an issue that I've been worried about since the merge because we didn’t really do it right, you know, the whole… "You're not my twin" “Hey, that's ok, close enough” plan? It worked which is, you know, cool. Hey. I'm even a little bit nice now. In case you were wondering. But I've been waiting for the issue to drop. And well I think it dropped. Because I'm- Where's the bathroom?"
Kai (to Jo): "I don't think you have food poisoning. I was supposed to merge my magic with you. But I got Luke's instead. Oh. And now I'm defective. And that’s why I think you're sick. Kind of feel like I’m dying actually. If I die, so do you, dad, Liv and the rest of our dumb coven. So, would you please fix me? Like, now?"
Kai (to Jo): "This is kind of private. Does your baby-boo need to be here?"
Kai (to Jo): "Yeah, duh. Because I'm magically diseased."
Kai (to Alaric): "You need to give me your magic. This faux merge is clearly falling because I was supposed to get your magic, right? Just- I don't know- Put it in a- Put it in a Teddy bear or a bed pan or whatever and gimmie!"
Kai (to Alaric): "I can see you're skeptical, Ric. Can I call you Ric?"
Kai (to Alaric): "If I die, the worlds collapse, all right? I see vacancy. Would you like me to start over with single syllables?"
Kai (to Jo): "Me, our coven, and the prison worlds thank you."
Kai (to Alaric): "A place filled with crappy people like me, I’m sure."
Kai (to Jo): "Oh. Don’t look so stressed."
Kai (to Jo): "Thank you. And congratulations. Have a good life, sissy."
- Let Her Go

Kai (to Damon): "I can't believe Bonnie made it out. Actually I can. She's plucky."
Kai (to Damon): "Hey, do you need help? Oh. Before you answer that, I’d rather not. Just keep experiencing these pangs of guilt watching you. Feelings are hard."
Kai (to Damon): "Damon, Bonnie saw her alive in a 1903 prison world. It's on camera. You want to watch it again?"
Kai (to Damon): "I'm just saying. Digging up mommy's grave? That's dark, even for me."
Kai (to Damon): "Mom's in a prison world and therefore an evil psychopath. Don't want to ruin little bro's perfect mommy memory."
Kai (to Damon): "Well, ever since you told me Bonnie was back, I, uh-, I can’t stop thinking about her."
Kai (to Damon): "I need to see her. I need to apologize. And you're gonna make that happen."
Kai (to Damon): "But there is a new me. You… you explained it to her so she would understand, right? Small words, easy to digest."
- The Downward Spiral

Kai (to Bonnie): "You want the 1903 ascendant. Well, sure. Just let me reach in my pocket and pull it out. Wait. Oh, that's weird. It was in my pocket."
Kai (to Bonnie): "I'll go if you go. Come on. It could be fun. You know, 1903, the gilded age. Didn't you ever dream about time travel?"
Kai (to Bonnie): "Damn. Crocodile Dundee called. He wants his knife back."
Kai (to Bonnie): "You have really nice palms."
Kai (to Bonnie): "Please! Believe me, I've changed."
- A Bird in a Gilded Cage

Kai: "It's time we get the hell out of this place."
- I'd Leave My Happy Home For You

Kai (to Bonnie): "Woah. You are not good at running."
Kai (to Bonnie): "No magic? Oh that's my fault. I was spooning you earlier. I think I might’ve sleep siphoned you. How you keep trying is just adorable like you're a having a seizure."
Kai (to Bonnie): "Did you think you could keep screwing people over and there wouldn't be any consequences?"
Kai: "I was gonna wait till the "death do us part" bit. But it seemed a little on the nose. Am I right?"
Kai: "Miss me? No? Oh, well."
- I'll Wed You in the Golden Summertime

Kai (to Stefan and Caroline): "Nothing personal, but this is a family matter now."
Kai: "Let me guess. Prison world? Ooh. But you can't kill me cause you all die too, right?"
Kai (to Alaric): "Hey, I'm sorry about your twinsies. I just don't feel like competing for leadership against future Gemini twins. See, when your family decides that you're nothing but an irredeemable piece of trash, well, guess the best thing to do is prove them right, right?"
Kai (to Joshua): "Here's to being different, dad."
Kai (to Alaric): "Bad time?"
Kai (to Alaric): "Freaky, right? I turned myself into one of Lily's Heretics. It's really incredible actually. I can literally siphon the magic of my vampirism and convert it into more magic
Kai (to Alaric): "Ouh. Looks like somebody's having a really bad day."
Kai: "Bad doggy."
Kai (to Bonnie through a camera): "All this time travel's has been hard on the camera, Bon. Yay! You saw the post-it. This message will self-destruct in ten seconds. Kidding. Anyhow, you're probably wondering why you're still alive, since I should have bled you out, one painful ounce at a time. I mean, that's what you deserved. You left me behind in 1903, which I did not appreciate, but I guess you forgot about that old Canadian rock filled with Bennett blood. Anyway, even though I got out, I kind of just want to make you suffer, in new and-- if I may say so myself-- totally inspired ways."
Kai(to Damon): "What's happening to me?"
Kai(to Damon): "It's just not as threatening when I'm seeing like, four super-blurry versions of you."
Kai: "Young, beautiful, human Elena Gilbert, preserved in this moment indefinitely."
Kai (to Bonnie through a camera): "So, Bonster, I linked Elena's life to yours. The rule is-- as long as you're alive, Elena will remain asleep."
Kai (to Bonnie through a camera): "And oh, please don't go looking for some weird witchy work-around, because as the incredibly-powerful leader of the Gemini's, I rigged this so that if you do try to outsmart it, both you and Elena will die-- instantly. I guess what I'm trying to say is your betrayal really hurt me, Bon. So, this is kind of all your fault."
Kai(to Damon): "Damon, think about it-- everyday that you wake up without Elena in your arms, you'll have the burning desire to kill Bonnie. Of course, you could just get it over with and kill her now, but Elena will probably never speak to you again."
Kai: "Hello! Anyone still alive, hm? Anyone alive, just raise your hand. I need blood."
Kai (to Bonnie): "Do your friends think you're funny? Because maybe if you were funny, if you were the one with the good jokes who they could always count on to make them laugh, maybe they'd be cool with letting you live instead of Elena."
Kai (to Bonnie): "I can't, what's done is done."
Kai (to Bonnie): "I can't undo the spell, Bonnie. My death made it permanent."
Kai (to Bonnie): "You know what's funny? I didn't even know werewolves were real until I got bit by one. The thing is, Bon-- the only way a guy turns into a wolf is if it's magic, right? So technically, their venom's magic, too. So I just went ahead and siphoned it up."
Kai(to Damon): "How dumb are you? I deliver you a dying Bonnie Bennett on a silver platter and woosh, right over your head."
Kai(to Damon): "Uh, translation: she's about to croak. Of course, you don't have to help her, you could just walk away. She dies of collapsed lung, no blood on your hands, and you and Elena get to live the life you always dreamed of. Either way, you better act quick."
Kai (to Bonnie): "That's it? He just left you? The whole point was that this will torture him for awhile. I mean, you'd think he'd at least flip a coin. Heads he picks you, tails he picks -"
- I'm Thinking Of You All The While


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References

See also